Dimethyl N-cyanodithioiminocarbonate → HCID 178503905, compound

HRID 2379837Notes

Reaction equation

HRID 2379837 reaction equation
[NH2:1][CH2:2][C:3]1[S:4][C:5]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)=[CH:6][N:7]=1.[CH3:17][S:18][C:19](SC)=[N:20][C:21]#[N:22]>C(O)C>[C:21]([N:20]=[C:19]([S:18][CH3:17])[NH:1][CH2:2][C:3]1[S:4][C:5]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)=[CH:6][N:7]=1)#[N:22]

Participants

4

Reactant 2

HCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 18953880HCID 18953880, compound

Product 1

HCID 178503905HCID 178503905, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(2-aminomethylthiazol-5-yl)-2-(diaminomethyleneamino)thiazole (0.45 g) and dimethyl N-cyanodithioiminocarbonate [(CH3S)2C=N-CN] (0.26 g) in ethanol (10 ml) was refluxed for 5 hours with stirring to give 4-[2-(3-cyano-2-methylisothioureido)methylthiazol-5-yl]-2-(diaminomethyleneamino)thiazole as a crude product. After cooling to ambient temperature, 40% aqueous methylamine by weight (1.4 ml) was added to the suspension and the mixture was stirred for 12 hours at ambient temperature. The solvent was evaporated in vacuo and the residue was mixed with water (5 ml) and ethyl acetate (5 ml). The resulting precipitate was collected and recrystallized from aqueous N,N-dimethylformamide to give 4-[2-(2-cyano-3-methylguanidino)methylthiazol-5-yl]-2-(diaminomethyleneamino)thiazole (0.35 g).

Workup

  1. temperaturewas refluxed for 5 hours

Sources & evidence

ORD record
ord-f271e47e273d4859b6a0784a994b8588
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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